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Sulfonium Acids Loaded onto an Unusual Thiotemplate Assembly Line Construct the Cyclopropanol Warhead of a Burkholderia Virulence Factor
Authors
Jakob Franke
Christian Hertweck
+6 more
Keishi Ishida
Mie Ishida-Ito
Hajo Kries
Georg Pohnert
Aleksa Stanišić
Felix Trottmann
Publication date
1 January 2020
Publisher
Weinheim : Wiley-VCH
Doi
Cite
Abstract
Pathogenic bacteria of the Burkholderia pseudomallei group cause severe infectious diseases such as glanders and melioidosis. Malleicyprols were identified as important bacterial virulence factors, yet the biosynthetic origin of their cyclopropanol warhead has remained enigmatic. By a combination of mutational analysis and metabolomics we found that sulfonium acids, dimethylsulfoniumpropionate (DMSP) and gonyol, known as osmolytes and as crucial components in the global organosulfur cycle, are key intermediates en route to the cyclopropanol unit. Functional genetics and in vitro analyses uncover a specialized pathway to DMSP involving a rare prokaryotic SET-domain methyltransferase for a cryptic methylation, and show that DMSP is loaded onto the NRPS-PKS hybrid assembly line by an adenylation domain dedicated to zwitterionic starter units. Then, the megasynthase transforms DMSP into gonyol, as demonstrated by heterologous pathway reconstitution in E. coli. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA
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Last time updated on 09/09/2020
Institutionelles Repositorium der Leibniz Universität Hannover
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Last time updated on 24/06/2021